β-sitosterol

Structural formula
General
Surname	β- sitosterol
other names	22,23-dihydrostigmasterine (24 R ) -24-ethyl-5-cholesten-3 β -ol 3 β -Stigmast-5-en-3-ol α- dihydrofucosterol Nimbosterol α- phytosterol Prostasal Quebrachol Rhamnol Cinchol Cupreol BETA-SITOSTEROL ( INCI )
Molecular formula	C 29 H 50 O
Brief description	colorless platelets
External identifiers / databases
CAS number 83-46-5 EC number 201-480-6 ECHA InfoCard 100.001.346 PubChem 222284 ChemSpider 192962 Wikidata Q121802
Drug information
Drug class	Cholesterol absorption inhibitors
properties
Molar mass	414.69 g mol −1
Physical state	firmly
Melting point	140 ° C
solubility	slightly soluble in water soluble in acetic acid , ethanol and ether
safety instructions
GHS labeling of hazardous substances no GHS pictograms H and P phrases H: no H-phrases P: no P-phrases
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

β-sitosterol , also β-sitosterol , belongs to the group of phytosterols , the chemical structure of which is similar to that of cholesterol . It's a white, waxy substance.

history

Sitosterol was first isolated from wheat germ oil in 1897 by Richard Burian , the founder of the Institute of Medical Physiology in Belgrade . He named it after its origin sitosterol ( English sitosterol ) ( ancient Greek σῖτος , sitos , "grain"). According to the work of Rudolph John Anderson, this sitosterol turned out to be a mixture with at least five components (α-sitosterol, β-sitosterol, γ-sitosterol, as well as stigmasterol and sitostanol ). Anderson was first able to isolate β-sitosterol in pure form from corn oil and wheat germ oil in 1926 .

Later research showed that Anderson's α-sitosterol is also a mixture of three components. In the years that followed, β-sitosterol was also found in many other vegetable oils.

Occurrence

β-sitosterol is widespread in the plant kingdom. At first it was in wheat germ oil, corn oil, rye germ oil , cottonseed oil , tall oil , in soybean oil and Calabarbohnen and in Cinchonawachs found leaves and bark (hence the name Cinchol ). But it also occurs in pecans , in the saw palmetto ( Serenoa repens ), in avocados ( Persea americana ), pumpkin seeds ( Curcurbita pepo ), Prunus africana ( Pygeum africanum ), cashew nuts , rice bran , sea buckthorn ( Hippophaë rhamnoides ) and buckthorn or buckthorn Goji fruits before.

Phytophagous insects cannot synthesize cholesterol and cover their needs through the intake of β-sitosterol or campesterol , which have to be dealkylated in the insect.

The highest concentrations of β-sitosterol can be found in the following parts of plants, given in parts per million :

• Cherimoya seeds ( Annona cherimola MILL.): 10,000-14,000 ppm
• Two-pronged hawthorn flowers and leaves ( Crataegus laevigata (POIR.) DC): 6500-7800 ppm in the flowers; 5100-6200 ppm in the leaves
• True black cumin seeds ( Nigella sativa L.): 3218 ppm
• Common evening primrose seeds ( Oenothera biennis L.): 1186-2528 ppm
• Sage leaves ( Salvia officinalis L.): 5-2450 ppm
• White mulberry ( Morus alba L.): 2000 ppm in the leaves
• Senna obtusifolia (L.) H. IRWIN & BARNEBY: 1000-2000 ppm in the seeds
• Buckwheat seeds ( Fagopyrum esculentum MOENCH.): 1880 ppm
• Basil leaves ( Ocimum basilicum L.): 896-1705 ppm
• Maize ( Zea mays L.): 1300 ppm in maize pen, in stigma / stylus (maize pen)
• Sage stem ( Salvia officinalis L.): 1214 ppm
• Basil flower ( Ocimum basilicum L.): 1051 ppm
• Sea buckthorn seeds ( Hippophae rhamnoides L.): 550-970 ppm
• Soybean ( Glycine max (L.) MERR.): 900 ppm in the seeds
• Licorice root ( Glycyrrhiza glabra L.): 500 ppm in Radix Liquiritiae
• Basil root ( Ocimum basilicum L.): 408 ppm
• Scented violets ( Viola odorata L.): 330 ppm in the plant
• Basil sprouts ( Ocimum basilicum L.): 230 ppm in the stem of the seedling
• Ashwaganda root, sleep berries -Wurzel ( Withania somnifera (L.) Dunal): 200 ppm
• Saw palmetto fruits, sabal palm ( Serenoa repens (W. BARTRAM) SMALL): 189 ppm

β-sitosterol content in some vegetable oils

source	Concentration in%	typical content in%
Tall oil	10-20	18th
Corn oil	0.5-1.0	0.9
Corn fiber oil	10-20	12.5
Pumpkin seed oil	0.2-0.3	0.25
Saw palmetto oil	0.1-0.3	0.2
Avocado oil	0.4-0.9	0.5
olive oil	0.2-0.3	0.2
Rice bran oil	0.5-0.8	0.75

properties

β-sitosterol is chiral . A diastereomer of β-sitosterol with (24 S ) configuration of the ethyl group in the side chain is called γ-sitosterol. The specific rotation value of β-sitosterol is −37 ° (c = 2.0 in chloroform at 25 ° C).

use

β-sitosterol is added to some types of margarine in a chemically modified form. Since it has only limited solubility in oils and fats (2-3%) and can be oxidized because of the double bond , the free β-sitosterol is hydrogenated and esterified with fatty acids (usually the fatty acid mixture from rapeseed oil ). Up to 8% of the product of this reaction is added to the spreadable fats under the name of stanol ester .

Pharmacological effect

The daily intake of β-sitosterol with food is approx. 250-300 mg, of which approx. 5% is absorbed in the gastrointestinal tract.

Like other phytosterols , β-sitosterol in higher doses (3–6 grams per day) reduces the absorption of cholesterol from the gastrointestinal tract . The aim is to lower the blood cholesterol level, the exact mechanism of action is not known. β-sitosterol is used as part of dietary measures for hypercholesterolemia in the form of appropriately fortified foods (e.g. margarine, dairy products). Accompanying medical treatment of high blood cholesterol with β-sitosterol when a low-fat and low-cholesterol diet alone is not sufficient is no longer relevant today.

Mainly in Germany, β-sitosterol is used as the main component of the substance "phytosterol", which is monographed in the European Pharmacopoeia, for the symptomatic treatment of the onset of benign prostatic hyperplasia (BPH). Studies have shown an improvement in the symptoms of BPH, but the prostate volume does not seem to decrease significantly. β-sitosterol has a weak anti-androgenic effect by inhibiting testosterone-5 α -reductase , which prevents the conversion of the sex hormone testosterone into the biologically active dihydrotestosterone . Also influencing the described prostaglandin the prostate : by β-sitosterol in vitro suppression of prostaglandin and was leukotriene synthesis and the arachidonic acid from cell membranes demonstrated. The tissue biopsy from the prostate adenoma showed a decrease in prostaglandin E ₂ and prostaglandin F _2α .

A smaller study showed an inhibition of baldness in men with saw palmetto extract .

In the case of treatments with sitosterol, it should be borne in mind that extensive studies on the genetically caused sitosterinemia are available. B. sitosterol, campesterol u. a. In the serum, after sufficient sample preparation, the coupling of capillary gas chromatography with mass spectrometry is available.

Trade names

Monopreparations

Harzol (D, A), Mutabella (D), Triastonal (D) and a generic (D)

Individual evidence

1. ↑ Entry on BETA-SITOSTEROL in the CosIng database of the EU Commission, accessed on February 16, 2020.
2. ↑ Entry on β-sitosterol. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
3. ↑ ^{a b c d} The Merck Index . 12th ed. Merck & Co. , Whitehouse Station, New Jersey, USA 1996.
4. ↑ ^{a b} Robert C. Weast (ed.): CRC Handbook of Chemistry and Physics . 58th edition. CRC Press, Cleveland, Ohio, USA 1977.
5. ↑ ^{a b} data sheet β-sitosterol from Sigma-Aldrich , accessed on February 7, 2019 ( PDF ).
6. ↑ Richard Burián: About Sitosterol . In: Monthly magazine for chemistry . tape 18 , no. 1 , December 1, 1897, p. 551-574 , doi : 10.1007 / BF01518263 ( PDF ).
7. ↑ RJ Anderson, RL Shriner: The Phytosterols of Corn Oil. In: Journal of the American Chemical Society. 48, 1926, pp. 2976-2986.
8. ↑ RJ Anderson, RL Shriner, GO Burr: The Phytosterols of Wheat Germ Oil. In: Journal of the American Chemical Society. 48, 1926, pp. 2987-2996.
9. ↑ Everett S. Wallis, E. Fernholz: α-Sitosterol. In: Journal of the American Chemical Society. 58, 1936, pp. 2446-2448.
10. ↑ Gerald Litwack: Insect Hormones . Gulf Professional Publishing, 2005, ISBN 0-12-709873-9 , pp. 33 ( limited preview in Google Book search).
11. ↑ Dr. Duke's Phytochemical and Ethnobotanical Databases: BETA-Sitosterol. accessed on February 5, 2018.
12. ↑ ^{a b c d} Laurence Eyres: Phytosterols and Other Functional Lipids in Food. ( Memento of October 8, 2011 in the Internet Archive ) Retrieved June 25, 2008.
13. ↑ ^{a b} K. Hardtke et al. (Ed.): Commentary on the European Pharmacopoeia Ph. Eur. 5.0. Phytosterol. Loose-leaf collection, 25th delivery, Wissenschaftliche Verlagsgesellschaft Stuttgart 2005.
14. ^ ^{A b} T. Dingermann, K. Hiller, G. Schneider, I. Zündorf: Schneider drug drugs. 5th edition. Elsevier 2004, ISBN 3-8274-1481-4 , pp. 238-239.
15. ↑ E. Mutschler, G. Geisslinger, HK Kroemer, P. Ruth, M. Schäfer-Korting: drug effects. Textbook of pharmacology and toxicology. 9th edition. Wissenschaftliche Verlagsgesellschaft, Stuttgart 2008, ISBN 978-3-8047-1952-1 , p. 710.
16. ↑ T. Wilt, A. Ishani, R. MacDonald, G. Stark, C. Mulrow, J. Lau: Beta-sitosterols for benign prostatic hyperplasia . In: Cochrane Database Syst Rev . No. 2 , 2000, pp. CD001043 , doi : 10.1002 / 14651858.CD001043 , PMID 10796740 .
17. ↑ N. Prager, K. Bickett, N. French, G. Marcovici: A randomized, double-blind, placebo-controlled trial to determine the effectiveness of botanically derived inhibitors of 5-alpha-reductase in the treatment of androgenetic alopecia. In: Journal of alternative and complementary medicine. 8, New York 2002, pp. 143-152; doi: 10.1089 / 107555302317371433 .
18. ↑ EG Yoo: Sitosterolemia: a review and update of pathophysiology, clinical spectrum, diagnosis, and management. In: Ann Pediatr Endocrinol Metab. 21 (1), Mar 2016, pp. 7-14. PMID 27104173
19. ↑ MD Shapiro: Rare Genetic Disorders Altering Lipoproteins. In: LJ De Groot, P. Beck-Peccoz, G. Chrousos, K. Dungan, A. Grossman, JM Hershman, C. Koch, R. McLachlan, M. New, R. Rebar, F. Singer, A. Vinik , MO Weickert (Ed.): Endotext [Internet]. South Dartmouth (MA): MDText.com. Inc .; 2000-. 2015 Jun 12. PMID 26561704
20. ↑ O. Weingärtner, D. Teupser, SB Patel: The Atherogenicity of Plant Sterols: The Evidence from Genetics to Clinical Trials. In: J AOAC Int. 98 (3), May-Jun 2015, pp. 742-749, Review. PMID 25942705
21. ↑ HS Ahmida, P. Bertucci, L. Franzò, R. Massoud, C. Cortese, A. Lala, G. Federici: Simultaneous determination of plasmatic phytosterols and cholesterol precursors using gas chromatography-mass spectrometry (GC-MS) with selective ion monitoring (SIM). In: J Chromatogr B Analyt Technol Biomed Life Sci. 842 (1), Sep 14, 2006, pp. 43-47. PMID 16807145

This article is about a health issue. It is not used for self-diagnosis and does not replace a diagnosis by a doctor. Please note the information on health issues !